Field of the Invention
This invention relates to a new quaternary ammonium salt, a process for preparing the same and a composition of the same useful for regulating plant growth.
Accordingly, the present invention provides, as a novel compound, a quaternary ammonium salt of the formula: ##SPC2##
Wherein A is a lower alkylene, a lower alkenylene or a lower alkadienylene; R.sub.1 and R.sub.2 are each lower alkyl which may be linked together directly or by an oxygen atom to form a saturated hetercyclic group; R.sub.3 is a lower alkyl, a halo(lower)alkyl, a lower alkynyl, a phenyl(lower)alkyl which may have one or more halogen atoms as substituents on the phenyl ring, a lower alkenyl, a hydroxy(lower)alkyl, a carboxy(lower)alkyl or a lower alkenyloxycarbonyl(lower)alkyl; R.sub.4, R.sub.5 and R.sub.6 are each lower alkyl having 1 to 3 carbon atoms; X is an acid residue; and a cyclohexyl ring in the above formula may have one double bond.
It is to be understood, within the scope of the present invention, that the term "lower" used in connection with alkyl, alkylene, etc. is intended to mean alkyl, alkylene, etc. having 1 to 10 carbon atoms unless otherwise indicated.
It is further to be understood, in this specification, that the lower alkylene covers methylene, ethylene, isopropylene, propylene, butylene, isobutylene, pentylene, etc.;
the lower alkenylene includes propenylene, 1-methyl-2-propenylene, 2-methyl-2-propenylene, 2-methyl-2-butenylene, etc; PA1 the lower alkaidenylene includes 2,4-pentadienylene, 3-methyl-2,4-pentadienylene, etc.; PA1 the lower alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl, heptyl, octyl, etc; PA1 the halo(lower)alkyl includes chloromethyl, bromoethyl, iodomethy., chloroethyl, bromoethyl, iodomethyl, fluoromethyl, fluoroethyl, dichloromethyl, dichloroethyl, dibromomethyl, diiodomethyl, diiodoethyl, chlorobromoethyl, chlorobromopropyl, chloropropyl, bromopropy, iodoisopropyl, etc.; PA1 the lower alkynyl includes ethynyl, 1-propynyl, 2-propynyl-(propargyl), 1-butynyl, 3-methyl-1-butynyl, 1-pentynyl, etc.; PA1 the phenyl(lower)alkyl includes benzyl, phenethyl, 3-phenylpropyl, etc.; PA1 the halogen includes fluorine, chlorine, bromine, bromine, iodine; PA1 the lower alkenyl includes vinyl, 1-propenyl, 2-propenyl-(alkyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, etc; PA1 the hydroxy(lower)alkyl includes hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 3-hydroxypropyl, 3-hydroxy-2-methylpropyl, 4-hydroxybutyl, 2-hydroxybutyl, etc; PA1 the carboxy(lower)alkyl includes carboxymethyl, 2-carboxyethyl, 3-carboxypropyl, 3-carboxy-2-methylpropyl, 4-carboxybutyl, etc,; PA1 the lower alkenyloxycarbonyl(lower)alkyl includes vinyloxycarbonylmethyl, vinyloxycarbonylethyl, propenyloxycarbonylmethyl, propenyloxycarbonylethyl, allyloxycarbonylmethyl, allyloxycarbonylethyl, allyloxycarbonylpropyl, propenyloxycarbonylpropyl, etc.; PA1 the acid residue includes chloride, iodide, bromide, etc.; PA1 the saturated heterocyclic group includes pyrrolidino, piperidino, morpholino, etc.; and PA1 the cyclohexyl ring in the above formula (I) which may have one double bond covers a cyclohexyl ring, for example, having the following formulae: ##SPC3## PA1 to prevent lodging of rice plant, wheat, etc. by inhibiting elongation; PA1 to dwarf the height of such vegetables as cucumber, tomato, egg-plant, soybean, peas, kidney bean, Spanish paprike, etc. and flowers such as cosmos, sage, chrysanthemum, cyclamene, poinsettia, stock, morning glory, etc.; PA1 to prevent overgrowth of a pericarp of citrus fruits such as mandarin, orange, etc.; PA1 to inhibit growth of a naught lateral branch of vegetables such as melon, water melon, cucumber, tomato, egg-plant, etc. and fruit trees such as pear, grape, apple, grapefruit, citrus fruits, etc.; PA1 to prevent ear germination of cereals such as rice plant, wheat, etc.; PA1 to accelerate enlargement in the root of edible roots such as radish, yam, onion, sweet potato, potato, chestnuts, carrot, burdock, etc.; PA1 to prevent bolting of vegetables such as cabbage, white rape, carrot, radish, spinach, burdock, etc.; PA1 to alleviate frost damage, damage from a drought, damage from a salty wind or damage from a hotness, of fruits such as Japanese persimmon, grape, mulberry, etc. and vegetables such as green pea, spinach, lettuce, etc.; PA1 to accelerate ripeness of fruits such as mandarin, apple, peach, grape, tomato, cherry, strawberry, etc.; PA1 to accelerate female flower bud formation of cucumber, water melon, melon, pumpkin, etc.; PA1 to induce flower-bud formation of flowers such as morning glory, cosmos, salvia, potmum, etc. and fruits such as apple, peach, grape, persimmon, etc. PA1 to prevent cracking of fruits such as grape, cherry, apple, etc.; PA1 to prevent overripening of water melon, melon, etc.; PA1 to prevent sprouting of plants such as potato, sweet potato, yam onion, chestnuts, etc. during storage thereof; PA1 to prevent generation and growth of auxilliary buds of tobacco plant, particularly after pinching of terminal bud; PA1 to improve storageability of cereals such as rice, wheat, corn, etc., fruits such as apple, chestnuts, etc., vegetables such as onion, yam, potato, sweet potato, etc., and other seeds or crops; PA1 to prevent malformation of egg-plants caused by side effect of some agricultural chemicals; PA1 to accelerate a vernalization, as control of a flower-bud formation, of plants such as grape, mandarin, apple, peach, barley, rye, wheat, etc.; PA1 to prevent dropping of fruits such as apple, mandarin, peach, pear, etc.
and a cyclohexenyl ring, for example, having the following formulae: ##SPC4##
wherein R.sub.4, R.sub.5 and R.sub.6 are each lower alkyl having 1 to 3 carbon atoms.
The quaternary ammonium salt of the formula (I) has a plant growth regulating activity. Specifically, it has a plant growth inhibiting activity due to its anti-gibberellin and anti-auxin action in a plant.
Accordingly, the compounds (I) can be used as growth regulators to artificially control the growth of plants in agriculture and horticulture, and may be useful in various applications typically illustrative as follows:
Use to prevent elongation in the height of plants such as Italian rye grass, orchard grass, sods, etc.;
The compound (I) may be further expected to be useful in various applications as follows:
Use to prevent head cracking of globose vegetables such as cabbage, etc.;